Hybrid Tetrameric Perylene Diimide Assemblies

Organic photovoltaics have found utility as indoor light recycling devices providing an opportunity for the sustainable powering of IoT sensors and related smart electronics. In the report, two organic pi-conjugated molecules consisting of four perylene diimide (PDI) chromophores each are presented and used as non-fullerene acceptors in indoor photovoltaic devices. The new materials consist of a dimeric N-annulated PDI core with single PDIs grafted onto the pyrrolic N-atom positions of the core. Compounds PDI(4)e and PDI(4)i are PDI tetramers and differ with PDI(4)e having the terminal N-annulated PDI with pyrrolic N-atom distal to the core and PDI(4)i having the terminal N-annulated PDI with pyrrolic N-atom proximal to the core. The structural and optoelectronic properties were investigated using NMR spectroscopy, optical absorption and emission spectroscopy, and cyclic voltammetry. The compounds exhibit typical optical signatures for PDIs but notable is that the addition of grafted PDI molecules prevents significant aggregation of the dimeric PDI core, as compared to a reference dimer. Use as non-fullerene acceptors in ternary bulk-heterojunction blends with the polymer FBT and fullerene PC61BM lead to increased open-circuit voltages and power conversion efficiencies upwards of 13.7 % at 2000 lux light intensity.